Isopropanol → rel-(2R,6S)-4-[1-(Diphenylmethyl)-3-azetidinyl]-2,6-dimethylmorpholine

HRID 1091297Notes

Reaction equation

HRID 1091297 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[CH3:23][C@H:24]1[O:29][C@@H:28]([CH3:30])[CH2:27][NH:26][CH2:25]1.CC(O)C.O1CCOCC1>C(OCC)(=O)C.[Cl-].[Na+].O>[CH:10]([N:8]1[CH2:9][CH:6]([N:26]2[CH2:25][C@H:24]([CH3:23])[O:29][C@H:28]([CH3:30])[CH2:27]2)[CH2:7]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 312751,4-DioxaneHCID 6415002,6-Dimethylmorpholine, cis-HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 66592200rel-(2R,6S)-4-[1-(Diphenylmethyl)-3-azetidinyl]-2,6-dimethylmorpholineYield 65%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Methanesulfonyloxy-1-benzhydrylazetidine (3.84 g, 12.1 mmol) and cis-2,6-dimethylmorpholine (6.97 mL, 60.5 mmol) were introduced into a screw vial, and IPA (10 mL) and dioxane (3 mL) were added thereto. The mixture was left to stand for 4 hours at 100° C. The reaction liquor was diluted with ethyl acetate, and saturated brine was added thereto. The mixture was partitioned. The obtained organic layer was washed with saturated brine, subsequently dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by column chromatography using silica gel (Flash Chromatography System from Biotage AB, column size: 40M, hexane/ethyl acetate=9:1 to 1:1), to obtain the title compound (2.63 g, 65%) as an oily matter.

Workup

  1. additionwere added
  2. waitThe mixture was left
  3. additionwas added
  4. customThe mixture was partitioned
  5. washThe obtained organic layer was washed with saturated brine
  6. dry with materialsubsequently dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7bf2bae3ee7c4bafb287346b1e1d549a
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

Loading…